Octacosanoic Acid
(Synonyms: 褐煤酸,Montanic acid) 目录号 : GC47815
A very long-chain saturated fatty acid
Cas No.:506-48-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Octacosanoic acid is a very long-chain saturated fatty acid. It is the major component of D-003, a mixture of very long-chain aliphatic acids purified from sugar cane wax that has antiplatelet and cholesterol-lowering activities in animal models.1
1.GÁmez, R., Rodeiro, I., FernÁndez, I., et al.Preliminary evaluation of the cytotoxic and genotoxic potential of D-003: Mixture of very long chain fatty acidsTeratog. Carcinoq. Mutagen.22(3)175-181(2002)
| Cas No. | 506-48-9 | SDF | |
| 别名 | 褐煤酸,Montanic acid | ||
| Canonical SMILES | CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O | ||
| 分子式 | C28H56O2 | 分子量 | 424.7 |
| 溶解度 | Chloroform: sparingly soluble,Ethanol: sparingly soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.3546 mL | 11.773 mL | 23.546 mL |
| 5 mM | 0.4709 mL | 2.3546 mL | 4.7092 mL |
| 10 mM | 0.2355 mL | 1.1773 mL | 2.3546 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
In vitro and in vivo study of octacosanol metabolism
Arch Med Res 2005 Mar-Apr;36(2):113-9.PMID:15847942DOI:10.1016/j.arcmed.2004.12.006.
Background: Policosanol is a mixture of very-long-chain aliphatic alcohols purified from sugar cane wax with cholesterol-lowering effects, whose main component is octacosanol. Scarce data about the metabolism of octacosanol and the other fatty alcohols composing policosanol have been published. Methods: Human fibroblasts were cultured in presence of (3)H-octacosanol during 0.5, 2 and 4 h. Lipid extracts were analyzed by thin layer chromatography, and the spots corresponding to octacosanol and Octacosanoic Acid were identified comparing with authentic standards. Spots were scraped, transferred to vials and radioactivity was measured. For corroborating the presence of octacosanol and Octacosanoic Acid, samples were analyzed by gas chromatography-mass spectrometry (GC-MS). The in vivo study of octacosanol metabolism was conducted in rats and Macaca arctoides monkeys. Rats were orally administered with policosanol (60 mg/kg) and free octacosanol and Octacosanoic Acid were identified in liver and plasma by GC-MS at various time intervals. Monkeys were orally and endovenously treated with policosanol (10 mg/kg) and the presence of free octacosanol, Octacosanoic Acid and some chain-shortened FA was investigated. Results: When fibroblasts were cultured in presence of (3)H-octacosanol, three spots were found: a first one corresponded to Octacosanoic Acid, a second to octacosanol and a third one remained unidentified. The radioactivity on the spot of Octacosanoic Acid slightly decreased throughout the incubation but increased in the third spot. Octacosanol and free octacosanoic acids were also identified in plasma of monkeys orally administered with policosanol. In addition, plasma samples showed free saturated acids, palmitic acid being the most abundant, followed by oleic and mystiric acids. Unsaturated acids (oleic and palmitoleic) were also observed. Conclusions: The present study demonstrates that Octacosanoic Acid is formed after incubation of fibroblast cultures with (3)H-octacosanol and after oral dosing with policosanol to rats. In addition, we demonstrated that shortened saturated (myristic, palmitic and stearic) and unsaturated (oleic, palmitoleic) FA are also formed after oral dosing with policosanol to monkeys. The present results are consistent with the fact that octacosanol metabolism is linked to FA metabolism via beta-oxidation, but further studies need to explore the occurrence of more metabolites proving such hypothesis.
The influence of the long chain fatty acid on the antagonistic activities of Rhizobium sin-1 lipid A
Bioorg Med Chem 2007 Jul 15;15(14):4800-12.PMID:17513113DOI:10.1016/j.bmc.2007.05.012.
The lipid A from nitrogen-fixing bacterial species Rhizobium sin-1 is structurally unusual due to lack of phosphates and the presence of a 2-aminogluconolactone and a very long chain fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0), moiety. This structurally unusual lipid A can antagonize TNF-alpha production by human monocytes induced by Escherichia coli LPS. To establish the relevance of the unusual long chain 27-hydroxyoctacosanoic acid for antagonistic properties, a highly convergent strategy for the synthesis of several derivatives of the lipid A of R. sin-1 has been developed. Compound 1 is a natural R. sin-1 lipid A having a 27-hydroxyoctacosanoic acid at C-2', compound 2 contains an Octacosanoic Acid moiety at this position, and compound 3 is modified by a short chain tetradecanoic acid. Cellular activation studies with a human monocytic cell line have shown that the Octacosanoic Acid is important for optimal antagonistic properties. The hydroxyl of the natural 27-hydroxyoctacosanoic moiety does, however, not account for inhibitory activity. The resulting structure-activity relationships are important for the design of compounds for the treatment of septic shock.
Comparison of three methods for the methylation of aliphatic and aromatic compounds
Rapid Commun Mass Spectrom 2017 Oct 15;31(19):1633-1640.PMID:28763166DOI:10.1002/rcm.7947.
Rationale: Methylation protocols commonly call for acidic, hot conditions that are known to promote organic 1 H/2 H exchange in aromatic and aliphatic C-H bonds. Here we tested two such commonly used methods and compared a third that avoids these acidic conditions, to quantify isotope effects with each method and to directly determine acidic-exchange rates relevant to experimental conditions. Methods: We compared acidic and non-acidic methylation approaches catalyzed by hydrochloric acid, acetyl chloride and EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide)/DMAP (4-dimethylaminopyridine), respectively. These were applied to two analytes: phthalic acid (an aromatic) and Octacosanoic Acid (an aliphatic). We analyzed yield by gas chromatography/flame ionization (GC/FID) and hydrogen and carbon isotopic compositions by isotope ratio mass spectrometry (GC/IRMS). We quantified the 1 H/2 H exchange rate on dimethyl phthalate under acidic conditions with proton nuclear magnetic resonance (1 H-NMR) measurements. Results: The δ2 H and δ13 C values and yield were equivalent among the three methods for methyl octacosanoate. The two acidic methods resulted in comparable yield and isotopic composition of dimethyl phthalate; however, the non-acidic method resulted in lower δ2 H and δ13 C values perhaps due to low yields. Concerns over acid-catalyzed 1 H/2 H exchange are unwarranted as the effect was trivial over a 12-h reaction time. Conclusions: We find product isolation yield and evaporation to be the main concerns in the accurate determination of isotopic composition. 1 H/2 H exchange reactions are too slow to cause measurable isotope fractionation over the typical duration and reaction conditions used in methylation. Thus, we are able to recommend continued use of acidic catalysts in such methylation reactions for both aliphatic and aromatic compounds.
Inhibition of saturated very-long-chain fatty acid biosynthesis by mefluidide and perfluidone, selective inhibitors of 3-ketoacyl-CoA synthases
Phytochemistry 2012 Apr;76:162-71.PMID:22284369DOI:10.1016/j.phytochem.2011.12.023.
The trifluoromethanesulphonanilides mefluidide and perfluidone are used in agriculture as plant growth regulators and herbicides. Despite the fact that mefluidide and perfluidone have been investigated experimentally for decades, their mode of action is still unknown. In this study, we used a cascade approach of different methods to clarify the mode of action and target site of mefluidide and perfluidone. Physiological profiling using an array of biotests and metabolic profiling in treated plants of Lemna paucicostata suggested a common mode of action in very-long-chain fatty acid (VLCFA) synthesis similar to the known 3-ketoacyl-CoA synthase (KCS) inhibitor metazachlor. Detailed analysis of fatty acid composition in Lemna plants showed a decrease of saturated VLCFAs after treatment with mefluidide and perfluidone. To study compound effects on enzyme level, recombinant KCSs from Arabidopsis thaliana were expressed in Saccharomyces cerevisiae. Enzyme activities of seven KCS proteins from 17 tested were characterized by their fatty acid substrate and product spectrum. For the KCS CER6, the VLCFA product spectrum in vivo, which consists of tetracosanoic acid, hexacosanoic acid and Octacosanoic Acid, is reported here for the first time. Similar to metazachlor, mefluidide and perfluidone were able to inhibit KCS1, CER6 and CER60 enzyme activities in vivo. FAE1 and KCS2 were inhibited by mefluidide only slightly, whereas metazachlor and perfluidone were strong inhibitors of these enzymes with IC(50) values in μM range. This suggests that KCS enzymes in VLCFA synthesis are the primary herbicide target of mefluidide and perfluidone.
Chemical constituents from the fruits of Hippophae rhamnoides
Nat Prod Res 2009;23(15):1451-6.PMID:19809919DOI:10.1080/14786410903075457.
Ten compounds were isolated from the fruits of Hippophae rhamnoides. On the basis of spectroscopic and chemical methods, the structures of these compounds were elucidated as hippophae cerebroside (1), oleanolic acid (2), ursolic acid (3), 19-alpha-hydroxyursolic acid (4), dulcioic acid (5), 5-hydroxymethyl-2-furancarbox-aldehyde (6), cirsiumaldehyde (7), Octacosanoic Acid (8), palmitic acid (9) and 1-O-hexadecanolenin (10). Among them, 1 was a new compound, and 4-7 and 10 were obtained from the genus for the first time.